Abstract : Although the American Civil War occurred over 130 years ago, analyses of failed campaigns provide insight and reinforce the importance of critical warfighting skills for today's strategic leader. Several principles in today's joint doctrine serve as excellent tools to analyze failed campaigns. This paper analyzes and identifies some of the reasons the Confederate Vicksburg Campaign failed. The paper examines Jefferson Davis's strategy, the Confederate command, control, and communications system, and the quality of the Confederate leadership. The paper concludes by showing how these three areas hindered the Confederate unity of effort and its implications for future strategic leaders.